DCT
1:19-cv-01240
Umicore Ag & Co KG v. Apeiron Synthesis SA
Key Events
Complaint
I. Executive Summary and Procedural Information
Parties & Counsel:
- Plaintiff: Umicore AG & Co. KG (Germany)
- Defendant: Apeiron Synthesis S.A. (Poland), Apeiron Synthesis, Inc. (Delaware), and Apeiron Catalysts SP ZOO (Poland)
- Plaintiff’s Counsel: Heyman Enerio Gattuso & Hirzel LLP; Leydig, Voit & Mayer, Ltd
Case Identification: [Umicore AG & Co. KG](https://ai-lab.exparte.com/party/umicore-ag) v. [Apeiron Synthesis S.A.](https://ai-lab.exparte.com/party/apeiron-synthesis-sa), et al., 1:19-cv-01240, D. Del., 06/28/2019
Venue Allegations: Plaintiff alleges venue is proper in the District of Delaware because Defendant Apeiron Synthesis, Inc. is a Delaware corporation, and because one or more of the Defendants are alleged to reside in, conduct business in, and have committed acts of infringement in the district.
Core Dispute: Plaintiff alleges that Defendant’s organometallic catalyst products, used for olefin metathesis, infringe five U.S. patents related to specific catalyst system compositions and structures.
Technical Context: The technology involves organometallic catalysts, specifically those using ruthenium, which are critical for olefin metathesis—a chemical process used to create specialized organic materials for industries including polymers, fuels, and pharmaceuticals.
Key Procedural History: The complaint alleges that Plaintiff holds rights to enforce the patents through a combination of exclusive licenses and acquisitions. Specifically, rights to the ’380 Patent were exclusively licensed from the University of New Orleans Research and Technology Foundation. Rights to the ’735 and ’255 Patents were obtained through Plaintiff's acquisition of Materia, Inc.'s metathesis catalyst IP and business portfolio, which included an exclusive license from the Trustees of Boston College. Rights to the ’843 and ’997 Patents were assigned to Plaintiff as part of the same acquisition from Materia.
Case Timeline
| Date | Event |
|---|---|
| 1998-09-10 | ’380 Patent Priority Date |
| 2000-08-10 | ’735 & ’255 Patents Priority Date |
| 2001-11-13 | ’380 Patent Issue Date |
| 2001-11-15 | ’843 & ’997 Patents Priority Date |
| 2003-07-11 | License agreement between Boston College and Materia, Inc. for ’735 and ’255 Patents |
| 2005-07-26 | ’735 Patent Issue Date |
| 2009-04-30 | License agreement between UNORF and Plaintiff for ’380 Patent |
| 2010-05-25 | ’255 Patent Issue Date |
| 2010-10-26 | ’843 Patent Issue Date |
| 2016-11-29 | ’997 Patent Issue Date |
| 2018-01-08 | Plaintiff acquires Materia's catalyst IP and obtains rights to the ’735, ’255, ’843, and ’997 Patents |
| 2019-02-11 | Defendants allegedly exhibit infringing products at a U.S. tradeshow |
| 2019-03-27 | Defendants allegedly present a webinar promoting infringing products to U.S. customers |
| 2019-06-28 | Complaint Filing Date |
II. Technology and Patent(s)-in-Suit Analysis
U.S. Patent No. 6,316,380 - "Catalyst System Comprising Transition Metal and Imidazoline-2-Ylidene or Imidazolidine-2-Ylidene"
The Invention Explained
- Problem Addressed: The patent’s background section notes that prior art methods for metal-catalyzed coupling reactions often rely on expensive, air-sensitive phosphine ligands and are generally unable to use aryl chlorides as a chemical feedstock, limiting their industrial and economic utility (’380 Patent, col. 1:30-49).
- The Patented Solution: The invention provides a catalyst system that combines a transition metal compound with an N-heterocyclic carbene, such as imidazoline-2-ylidene (’380 Patent, col. 1:65-2:5). These carbenes are described as "phosphine mimics" that are more thermally stable and less likely to dissociate from the metal center, overcoming the instability of prior art catalysts (’380 Patent, col. 1:52-64). A key feature of the claimed carbene is the presence of bulky aromatic groups on the nitrogen atoms, which are themselves substituted at their ortho positions with secondary or tertiary groups, enhancing the catalyst's effectiveness (’380 Patent, col. 2:12-19).
- Technical Importance: This approach offered a more robust and versatile catalyst system for important chemical coupling reactions, potentially enabling the use of less expensive starting materials like aryl chlorides (’380 Patent, col. 1:35-40).
Key Claims at a Glance
- The complaint asserts independent claim 1 and dependent claims, with a specific infringement example for dependent claim 11 (Compl. ¶60-61).
- Independent Claim 1, as relevant to the infringement allegations for Claim 11, requires:
- A composition which comprises
- at least one metal compound comprising at least one transition metal atom; and
- at least one N-heterocyclic carbene selected from the group consisting of... an imidazolidine-2-ylidene wherein the 1 and 3 positions are each, independently, substituted by an aromatic group in which each ortho position is, independently, substituted by a secondary or tertiary group having at least three atoms, or a protonated salt of such an imidazolidine-2-ylidene.
U.S. Patent No. 6,921,735 - "Recyclable Metathesis Catalysts"
The Invention Explained
- Problem Addressed: The patent’s background section highlights that while organometallic ruthenium-based catalysts are effective for olefin metathesis, their cost and the risk of metal contamination in the final product make catalyst recovery and reuse critically important (’735 Patent, col. 1:26-37). Existing recyclable catalysts were identified as having shortcomings, such as being useful primarily for substrates with terminal alkenes (’735 Patent, col. 1:41-45).
- The Patented Solution: The invention discloses a class of highly active, recoverable, and recyclable transition metal catalysts. The patented catalyst structure features a transition metal (e.g., Ruthenium) complexed with both an electron-donating heterocyclic carbene ligand and a specific organic ligand (a styrenyl ether) that allows for the catalyst to be easily recovered from the reaction mixture, for instance via silica gel chromatography (’735 Patent, Abstract; col. 2:1-4). This design enhances catalytic activity while enabling reuse, addressing both cost and contamination concerns.
- Technical Importance: The invention provided a practical solution for making expensive but powerful metathesis catalysts more economically viable and environmentally friendly by enabling their efficient recovery and reuse in subsequent reactions (’735 Patent, col. 2:1-4).
Key Claims at a Glance
- The complaint asserts independent claim 1 and dependent claims, with a specific infringement example for dependent claim 5 (Compl. ¶70-71).
- Independent Claim 1 requires:
- A transition metal catalyst having a specific chemical structure (Formula I) comprising:
- A transition metal, M
- A heteroatom, X (e.g., oxygen)
- An electron withdrawing anionic ligand, R1 and R2
- An electron-donating heterocyclic carbene ligand, Y
- A substituent R (e.g., alkyl)
- Substituents a, b, c, and d on the aromatic ring
U.S. Patent No. 7,723,255 - "Recyclable Metathesis Catalysts"
- Technology Synopsis: As a divisional of the ’735 patent, this patent addresses the same technical problem of creating recoverable and reusable metathesis catalysts. The solution is also a transition metal complex with a specific ligand structure that facilitates both high catalytic activity and recovery from the reaction mixture (’255 Patent, col. 1:15-49).
- Asserted Claims: The complaint asserts at least Claims 1, 4, 5, 18, and 20-28, with a specific example focusing on independent claim 20 (Compl. ¶85-87).
- Accused Features: The complaint alleges that the accused catalyst StickyCat PF6 has the chemical structure claimed in the ’255 Patent (Compl. ¶86).
U.S. Patent No. 7,820,843 - "Chelating Carbene Ligand Precursors and Their Use in the Synthesis of Metathesis Catalysts"
- Technology Synopsis: This patent is directed to chelating carbene ligands for preparing olefin metathesis catalysts that are air-stable and can be recovered and reused. The invention uses internal olefin compounds (beta-substituted styrenes) as ligand precursors, which are described as being more stable and less costly to prepare than the terminal olefins used in prior art methods (’843 Patent, Abstract).
- Asserted Claims: The complaint asserts at least Claims 1, 4, 5, and 6, with a specific example focusing on independent claim 1 (Compl. ¶100-102).
- Accused Features: The complaint alleges that the accused catalyst HeatMet embodies the claimed chelating carbine complex structure (Compl. ¶101, 103).
U.S. Patent No. 9,504,997 - "Chelating Carbene Ligand Precursors and Their Use in the Synthesis of Metathesis Catalysts"
- Technology Synopsis: Related to the ’843 Patent, this patent is also directed to stable, recoverable olefin metathesis catalysts synthesized using chelating carbene ligand precursors. The technology aims to provide efficient synthesis routes for these valuable catalysts, which can be crystallized from an organic solvent without the need for purification methods like chromatography that are less suitable for large-scale production (’997 Patent, Abstract).
- Asserted Claims: The complaint asserts at least Claims 1, 4, 5, and 6, with a specific example focusing on independent claim 1 (Compl. ¶116-118).
- Accused Features: The complaint alleges that the accused catalyst nitro-Grela has the chemical structure of the claimed chelating carbine complex (Compl. ¶117, 119).
III. The Accused Instrumentality
Product Identification
The complaint accuses at least 29 distinct catalyst products (the "Infringing Catalysts") and several catalyst kits (the "Infringing Kits") (Compl. ¶28-29). Specific examples used to illustrate infringement include GreenCat, StickyCat PF6, HeatMet, and nitro-Grela (Compl. ¶61, 71, 101, 117).
Functionality and Market Context
The accused products are organometallic catalysts sold for use in olefin metathesis, a chemical synthesis process (Compl. ¶12, 14). The complaint alleges Defendants market these products in the United States through their website, at U.S. tradeshows, and via U.S.-based distributors including Sigma-Aldrich, TCI America, and Strem Chemicals (Compl. ¶30, 33, 37). The complaint provides detailed pricing and quantity information from distributor websites, suggesting commercial availability to U.S. customers (Compl. ¶40, 45, 50, Tables 1-3). A screenshot from Defendants' website shows contact information for a U.S. representative in Cambridge, MA, to facilitate direct purchases (Compl. ¶31).
IV. Analysis of Infringement Allegations
’380 Patent Infringement Allegations
| Claim Element (from Independent Claim 1, via Dependent Claim 11) | Alleged Infringing Functionality | Complaint Citation | Patent Citation |
|---|---|---|---|
| a composition which comprises... at least one metal compound comprising at least one transition metal atom | The accused product GreenCat is a chemical compound that contains ruthenium (Ru), which is a transition metal. | ¶62 | col. 3:6-12 |
| and at least one N-heterocyclic carbene selected from the group consisting of... an imidazolidine-2-ylidene wherein the 1 and 3 positions are each, independently, substituted by an aromatic group... | GreenCat is alleged to include an N-heterocyclic carbene (imidazolidine-2-ylidene) as part of its molecular structure. A diagram in the complaint highlights this specific portion of the GreenCat molecule (Compl. p. 19). | ¶63 | col. 3:15-24 |
| ...in which each ortho position is, independently, substituted by a secondary or tertiary group having at least three atoms | The aromatic groups on the N-heterocyclic carbene in GreenCat are alleged to be 2,6-diisopropylphenyl groups, which satisfy this limitation. | ¶64 | col. 3:19-24 |
| [from Claim 11] said disubstituted phenyl group is a 2,6-diisopropylphenyl group | GreenCat is alleged to include 2,6-diisopropylphenyl groups. A diagram in the complaint circles the entire N-heterocyclic carbene ligand, including these specific groups (Compl. p. 20). | ¶64 | col. 13:19-22 |
- Identified Points of Contention:
- Scope Questions: The complaint alleges the accused group is a "1,6-diisopropylphenyl group" (Compl. ¶64), whereas the patent claim language specifies a "2,6-diisopropylphenyl group" ('380 Patent, col. 13:21-22). This appears to be a typographical error in the complaint, but it raises the question of whether there is any ambiguity in the accused product's actual structure that could be material to the infringement analysis.
- Technical Questions: The analysis will depend on factual evidence confirming that the chemical structure of the marketed GreenCat product is identical to the structure depicted in the complaint and that it meets the specific definitions for "imidazolidine-2-ylidene" and "aromatic group" as construed from the patent.
’735 Patent Infringement Allegations
| Claim Element (from Independent Claim 1, via Dependent Claim 5) | Alleged Infringing Functionality | Complaint Citation | Patent Citation |
|---|---|---|---|
| a transition metal catalyst having the following structure: [Formula I] | The accused catalyst StickyCat PF6 is alleged to have the overall molecular structure depicted in Formula I. The complaint provides a labeled drawing of the generic structure from the patent and a corresponding drawing of the accused product (Compl. p. 21). | ¶72-73 | col. 5:10-50 |
| M comprises a transition metal | StickyCat PF6 is alleged to contain a ruthenium (Ru) atom, which is a transition metal, at the M position. | ¶74 | col. 5:21 |
| R1 and R2 each comprises... an electron withdrawing anionic ligand | The R1 and R2 positions in StickyCat PF6 are alleged to be occupied by chlorine atoms, which are electron withdrawing anionic ligands. | ¶75 | col. 5:30-32 |
| Y comprises an electron-donating heterocyclic carbene ligand | StickyCat PF6 is alleged to include a specific electron-donating heterocyclic carbene ligand at the Y position. | ¶76 | col. 6:40-42 |
| X comprises oxygen | StickyCat PF6 is alleged to have an oxygen atom at the X position. | ¶77 | col. 5:23 |
| [from Claim 5] R is isopropyl | StickyCat PF6 is alleged to contain an isopropyl group at the R position. | ¶78 | col. 38:6-7 |
| a, b, c, and d each comprise H | The accused product is alleged to include hydrogen (H) atoms at each of the positions corresponding to a, b, c, and d. | ¶79 | col. 5:33-34 |
- Identified Points of Contention:
- Scope Questions: A central question may be how broadly the term "electron-donating heterocyclic carbene ligand" is construed. Infringement will depend on whether the specific ligand in StickyCat PF6, as factually determined, falls within the scope of this term as defined by the patent's specification.
- Technical Questions: What evidence confirms that the accused StickyCat PF6 product contains all elements of the claimed structure in the specified positions? The complaint's infringement theory rests on a direct, element-by-element structural match, which will require factual proof beyond the diagrams presented.
V. Key Claim Terms for Construction
For the ’380 Patent:
- The Term: "a secondary or tertiary group having at least three atoms"
- Context and Importance: This term defines the required steric bulk on the aromatic groups attached to the N-heterocyclic carbene. The infringement allegation against GreenCat hinges on its diisopropylphenyl groups meeting this definition. Practitioners may focus on this term because the patent emphasizes the importance of these bulky groups for achieving the invention's catalytic advantages.
- Intrinsic Evidence for Interpretation:
- Evidence for a Broader Interpretation: The specification provides a non-exhaustive list of examples, including "isopropyl, cyclopropyl, sec-butyl, tert-butyl, cyclobutyl, 3-pentyl, cyclopentyl, cyclohexyl," suggesting the term covers a range of common chemical groups (’380 Patent, col. 4:55-59).
- Evidence for a Narrower Interpretation: The patent consistently frames these groups in the context of their steric properties and their role in enhancing catalyst performance. An argument could be made that the term should be limited to groups that achieve a specific level of steric hindrance taught in the specification, potentially excluding groups that are structurally different from the preferred embodiments.
For the ’735 Patent:
- The Term: "electron-donating heterocyclic carbene ligand"
- Context and Importance: This ligand is a core component of the claimed catalyst, credited with significantly enhancing its activity (’735 Patent, Abstract). The infringement allegation against StickyCat PF6 requires its corresponding molecular fragment to be classified as such. The precise electronic and structural properties required to meet this definition will be critical.
- Intrinsic Evidence for Interpretation:
- Evidence for a Broader Interpretation: Claim 1 recites the term generically without limiting it to a specific structure, suggesting it covers any heterocyclic carbene ligand that performs the function of donating electrons to the metal center (’735 Patent, col. 6:40-42).
- Evidence for a Narrower Interpretation: The specification provides a preferred embodiment of this ligand as a "4,5-dihydroimidazol-2-ylidene carbene ligand ring structure" (Formula II) with specific aromatic ring moieties (R3 and R4), such as 2,4,6-trimethylphenyl (’735 Patent, col. 6:44-65). A defendant may argue that the term should be construed as limited to this specific class of structures explicitly disclosed and exemplified.
VI. Other Allegations
- Willful Infringement: The complaint alleges willful infringement for all five patents-in-suit (Compl. ¶65, 80, 95, 111, 127). The allegations of knowledge are based on specific pre-suit events:
- Defendants’ own U.S. Patent No. 9,527,877 allegedly cites the ’843 Patent as prior art, providing knowledge of the ’843 and related ’997 Patents (Compl. ¶56).
- Defendants’ website allegedly references a PCT application related to the ’735 and ’255 Patents (Compl. ¶57).
- A key employee of Defendants, Dr. Karol Grela, allegedly worked with a co-inventor of the ’380 Patent on related research, providing knowledge of that patent (Compl. ¶58).
VII. Analyst’s Conclusion: Key Questions for the Case
This case presents a direct structural infringement dispute in the specialized field of organometallic chemistry. The central questions for the court will likely be:
- A core issue will be one of claim construction: How will the court define key technical terms such as "secondary or tertiary group having at least three atoms" (’380 Patent) and "electron-donating heterocyclic carbene ligand" (’735 Patent)? The outcome of the infringement analysis will depend heavily on whether the specific molecular fragments of the accused products fall within the construed scope of these terms.
- A key evidentiary question will be one of structural identity: What factual proof will be presented to confirm that the chemical compositions of the catalyst products sold by Defendants in the U.S. are identical to the structures depicted in the complaint and claimed in the patents? The case hinges on a direct, one-to-one mapping of claimed chemical structures to accused products.
- A significant issue for damages will be willfulness: The complaint pleads pre-suit knowledge with a high degree of specificity, citing Defendants' own patent filings and employee history. The question will be whether these allegations are sufficient to establish the knowledge and intent required for a finding of willful infringement, which could expose Defendants to enhanced damages.